TWI603946B - Aniline derivatives, charge-transporting varnishes and organic electroluminescent devices - Google Patents
Aniline derivatives, charge-transporting varnishes and organic electroluminescent devices Download PDFInfo
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- TWI603946B TWI603946B TW103121348A TW103121348A TWI603946B TW I603946 B TWI603946 B TW I603946B TW 103121348 A TW103121348 A TW 103121348A TW 103121348 A TW103121348 A TW 103121348A TW I603946 B TWI603946 B TW I603946B
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- 239000002966 varnish Substances 0.000 title claims description 69
- 125000002490 anilino group Chemical class [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 title description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 124
- -1 thiol Alcohol group Chemical group 0.000 claims description 121
- 150000001448 anilines Chemical class 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- 125000005843 halogen group Chemical group 0.000 claims description 50
- 238000000034 method Methods 0.000 claims description 42
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 37
- 125000003118 aryl group Chemical group 0.000 claims description 36
- 239000002253 acid Substances 0.000 claims description 31
- 229910052799 carbon Inorganic materials 0.000 claims description 31
- 239000002019 doping agent Substances 0.000 claims description 27
- 238000002347 injection Methods 0.000 claims description 24
- 239000007924 injection Substances 0.000 claims description 24
- 125000001072 heteroaryl group Chemical group 0.000 claims description 22
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 17
- 125000000304 alkynyl group Chemical group 0.000 claims description 16
- 239000003960 organic solvent Substances 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 239000000126 substance Substances 0.000 claims description 14
- 125000001424 substituent group Chemical group 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 13
- 125000003172 aldehyde group Chemical group 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000005017 substituted alkenyl group Chemical group 0.000 claims description 12
- 125000000542 sulfonic acid group Chemical group 0.000 claims description 11
- 125000002843 carboxylic acid group Chemical group 0.000 claims description 10
- 230000005525 hole transport Effects 0.000 claims description 10
- 125000002577 pseudohalo group Chemical group 0.000 claims description 8
- 125000004426 substituted alkynyl group Chemical group 0.000 claims description 7
- 238000005401 electroluminescence Methods 0.000 claims description 5
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 2
- 239000010410 layer Substances 0.000 description 58
- 229910052757 nitrogen Inorganic materials 0.000 description 28
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 239000002904 solvent Substances 0.000 description 26
- 150000001875 compounds Chemical class 0.000 description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 24
- 239000000243 solution Substances 0.000 description 20
- 239000000758 substrate Substances 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
- 229910052707 ruthenium Inorganic materials 0.000 description 18
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 17
- 229910052731 fluorine Inorganic materials 0.000 description 16
- 125000001153 fluoro group Chemical group F* 0.000 description 16
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 16
- 125000003342 alkenyl group Chemical group 0.000 description 15
- 238000000576 coating method Methods 0.000 description 15
- KDLHZDBZIXYQEI-UHFFFAOYSA-N palladium Substances [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 15
- 229940125904 compound 1 Drugs 0.000 description 14
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 14
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical class NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 12
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- 239000007983 Tris buffer Substances 0.000 description 12
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 12
- 239000011964 heteropoly acid Substances 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000000203 mixture Substances 0.000 description 12
- 238000004519 manufacturing process Methods 0.000 description 11
- 239000012299 nitrogen atmosphere Substances 0.000 description 11
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 10
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- FSEXLNMNADBYJU-UHFFFAOYSA-N 2-phenylquinoline Chemical compound C1=CC=CC=C1C1=CC=C(C=CC=C2)C2=N1 FSEXLNMNADBYJU-UHFFFAOYSA-N 0.000 description 8
- 238000005259 measurement Methods 0.000 description 8
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 8
- 238000006467 substitution reaction Methods 0.000 description 8
- 229910052782 aluminium Inorganic materials 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 235000010290 biphenyl Nutrition 0.000 description 7
- 238000001914 filtration Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 239000011248 coating agent Substances 0.000 description 6
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 239000012044 organic layer Substances 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 238000007789 sealing Methods 0.000 description 6
- 238000003786 synthesis reaction Methods 0.000 description 6
- DQGPWNBGAYGUPK-UHFFFAOYSA-N 1,1,1-trifluoro-4-(trimethoxymethyl)dodecane Chemical compound FC(CCC(C(OC)(OC)OC)CCCCCCCC)(F)F DQGPWNBGAYGUPK-UHFFFAOYSA-N 0.000 description 5
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 5
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical group CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 229910052787 antimony Inorganic materials 0.000 description 5
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 238000010304 firing Methods 0.000 description 5
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 5
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 5
- 238000001840 matrix-assisted laser desorption--ionisation time-of-flight mass spectrometry Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- DHRLEVQXOMLTIM-UHFFFAOYSA-N phosphoric acid;trioxomolybdenum Chemical compound O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.O=[Mo](=O)=O.OP(O)(O)=O DHRLEVQXOMLTIM-UHFFFAOYSA-N 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 5
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- UXKQNCDDHDBAPD-UHFFFAOYSA-N 4-n,4-n-diphenylbenzene-1,4-diamine Chemical compound C1=CC(N)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 UXKQNCDDHDBAPD-UHFFFAOYSA-N 0.000 description 4
- JSGRIFNBTXDZQU-UHFFFAOYSA-N C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC Chemical compound C1(=CC=CC=C1)C(C(OC)(OC)OC)CCCCCCCC JSGRIFNBTXDZQU-UHFFFAOYSA-N 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 239000013065 commercial product Substances 0.000 description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical group C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 4
- 239000002861 polymer material Substances 0.000 description 4
- BPEVHDGLPIIAGH-UHFFFAOYSA-N ruthenium(3+) Chemical compound [Ru+3] BPEVHDGLPIIAGH-UHFFFAOYSA-N 0.000 description 4
- 238000000926 separation method Methods 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 238000004528 spin coating Methods 0.000 description 4
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical class C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 4
- 229920002554 vinyl polymer Polymers 0.000 description 4
- ONUFSRWQCKNVSL-UHFFFAOYSA-N 1,2,3,4,5-pentafluoro-6-(2,3,4,5,6-pentafluorophenyl)benzene Chemical group FC1=C(F)C(F)=C(F)C(F)=C1C1=C(F)C(F)=C(F)C(F)=C1F ONUFSRWQCKNVSL-UHFFFAOYSA-N 0.000 description 3
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- LPCWDYWZIWDTCV-UHFFFAOYSA-N 1-phenylisoquinoline Chemical compound C1=CC=CC=C1C1=NC=CC2=CC=CC=C12 LPCWDYWZIWDTCV-UHFFFAOYSA-N 0.000 description 3
- RICKKZXCGCSLIU-UHFFFAOYSA-N 2-[2-[carboxymethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]ethyl-[[3-hydroxy-5-(hydroxymethyl)-2-methylpyridin-4-yl]methyl]amino]acetic acid Chemical compound CC1=NC=C(CO)C(CN(CCN(CC(O)=O)CC=2C(=C(C)N=CC=2CO)O)CC(O)=O)=C1O RICKKZXCGCSLIU-UHFFFAOYSA-N 0.000 description 3
- YPIANBZIVBPMJS-UHFFFAOYSA-N 2-bromo-n,n-diphenylaniline Chemical compound BrC1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPIANBZIVBPMJS-UHFFFAOYSA-N 0.000 description 3
- VQGHOUODWALEFC-UHFFFAOYSA-N 2-phenylpyridine Chemical compound C1=CC=CC=C1C1=CC=CC=N1 VQGHOUODWALEFC-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000208340 Araliaceae Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 3
- 235000005035 Panax pseudoginseng ssp. pseudoginseng Nutrition 0.000 description 3
- 235000003140 Panax quinquefolius Nutrition 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- HASCQPSFPAKVEK-UHFFFAOYSA-N dimethyl(phenyl)phosphine Chemical compound CP(C)C1=CC=CC=C1 HASCQPSFPAKVEK-UHFFFAOYSA-N 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 235000008434 ginseng Nutrition 0.000 description 3
- 239000012535 impurity Substances 0.000 description 3
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 3
- 239000011261 inert gas Substances 0.000 description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 150000004715 keto acids Chemical class 0.000 description 3
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 3
- 229910052750 molybdenum Inorganic materials 0.000 description 3
- 239000011733 molybdenum Substances 0.000 description 3
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical compound C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229910052763 palladium Inorganic materials 0.000 description 3
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 3
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000010992 reflux Methods 0.000 description 3
- YAYGSLOSTXKUBW-UHFFFAOYSA-N ruthenium(2+) Chemical compound [Ru+2] YAYGSLOSTXKUBW-UHFFFAOYSA-N 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 229910052938 sodium sulfate Inorganic materials 0.000 description 3
- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 125000005504 styryl group Chemical group 0.000 description 3
- 125000003107 substituted aryl group Chemical group 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- 238000001308 synthesis method Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 3
- 229910052721 tungsten Inorganic materials 0.000 description 3
- 239000010937 tungsten Substances 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- XDPNCTNYEDMQEN-UHFFFAOYSA-N (1,1,1-triethoxy-2,3,3,4,4-pentafluorodecan-2-yl)benzene Chemical compound FC(C(C(C(OCC)(OCC)OCC)(C1=CC=CC=C1)F)(F)F)(CCCCCC)F XDPNCTNYEDMQEN-UHFFFAOYSA-N 0.000 description 2
- 239000001211 (E)-4-phenylbut-3-en-2-one Substances 0.000 description 2
- DCTMXCOHGKSXIZ-UHFFFAOYSA-N (R)-1,3-Octanediol Chemical compound CCCCCC(O)CCO DCTMXCOHGKSXIZ-UHFFFAOYSA-N 0.000 description 2
- CWZQYRJRRHYJOI-UHFFFAOYSA-N 1,1,1-trimethoxydecane Chemical compound CCCCCCCCCC(OC)(OC)OC CWZQYRJRRHYJOI-UHFFFAOYSA-N 0.000 description 2
- FYGHSUNMUKGBRK-UHFFFAOYSA-N 1,2,3-trimethylbenzene Chemical compound CC1=CC=CC(C)=C1C FYGHSUNMUKGBRK-UHFFFAOYSA-N 0.000 description 2
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- OWBTYPJTUOEWEK-UHFFFAOYSA-N butane-2,3-diol Chemical compound CC(O)C(C)O OWBTYPJTUOEWEK-UHFFFAOYSA-N 0.000 description 1
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003729 cation exchange resin Substances 0.000 description 1
- GWXLDORMOJMVQZ-UHFFFAOYSA-N cerium Chemical compound [Ce] GWXLDORMOJMVQZ-UHFFFAOYSA-N 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 238000010549 co-Evaporation Methods 0.000 description 1
- 229910017052 cobalt Inorganic materials 0.000 description 1
- 239000010941 cobalt Substances 0.000 description 1
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 150000004696 coordination complex Chemical class 0.000 description 1
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 1
- GBRBMTNGQBKBQE-UHFFFAOYSA-L copper;diiodide Chemical compound I[Cu]I GBRBMTNGQBKBQE-UHFFFAOYSA-L 0.000 description 1
- VBVAVBCYMYWNOU-UHFFFAOYSA-N coumarin 6 Chemical compound C1=CC=C2SC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 VBVAVBCYMYWNOU-UHFFFAOYSA-N 0.000 description 1
- 125000006165 cyclic alkyl group Chemical group 0.000 description 1
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- ARUKYTASOALXFG-UHFFFAOYSA-N cycloheptylcycloheptane Chemical group C1CCCCCC1C1CCCCCC1 ARUKYTASOALXFG-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- WVIIMZNLDWSIRH-UHFFFAOYSA-N cyclohexylcyclohexane Chemical group C1CCCCC1C1CCCCC1 WVIIMZNLDWSIRH-UHFFFAOYSA-N 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical group C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- MAWOHFOSAIXURX-UHFFFAOYSA-N cyclopentylcyclopentane Chemical group C1CCCC1C1CCCC1 MAWOHFOSAIXURX-UHFFFAOYSA-N 0.000 description 1
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
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- 229940019778 diethylene glycol diethyl ether Drugs 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- SBZXBUIDTXKZTM-UHFFFAOYSA-N diglyme Chemical compound COCCOCCOC SBZXBUIDTXKZTM-UHFFFAOYSA-N 0.000 description 1
- XUCJHNOBJLKZNU-UHFFFAOYSA-M dilithium;hydroxide Chemical compound [Li+].[Li+].[OH-] XUCJHNOBJLKZNU-UHFFFAOYSA-M 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- GPAYUJZHTULNBE-UHFFFAOYSA-O diphenylphosphanium Chemical compound C=1C=CC=CC=1[PH2+]C1=CC=CC=C1 GPAYUJZHTULNBE-UHFFFAOYSA-O 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- CJMZLCRLBNZJQR-UHFFFAOYSA-N ethyl 2-amino-4-(4-fluorophenyl)thiophene-3-carboxylate Chemical compound CCOC(=O)C1=C(N)SC=C1C1=CC=C(F)C=C1 CJMZLCRLBNZJQR-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000003682 fluorination reaction Methods 0.000 description 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 1
- 229910052733 gallium Inorganic materials 0.000 description 1
- 229910052732 germanium Inorganic materials 0.000 description 1
- GNPVGFCGXDBREM-UHFFFAOYSA-N germanium atom Chemical compound [Ge] GNPVGFCGXDBREM-UHFFFAOYSA-N 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- VBJZVLUMGGDVMO-UHFFFAOYSA-N hafnium atom Chemical compound [Hf] VBJZVLUMGGDVMO-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- ITIDSNKGTOBPBD-UHFFFAOYSA-N hydroxy-phenyl-sulfanyl-sulfanylidene-$l^{5}-phosphane Chemical compound OP(S)(=S)C1=CC=CC=C1 ITIDSNKGTOBPBD-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 229910052738 indium Inorganic materials 0.000 description 1
- APFVFJFRJDLVQX-UHFFFAOYSA-N indium atom Chemical compound [In] APFVFJFRJDLVQX-UHFFFAOYSA-N 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- YERGTYJYQCLVDM-UHFFFAOYSA-N iridium(3+);2-(4-methylphenyl)pyridine Chemical compound [Ir+3].C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1.C1=CC(C)=CC=C1C1=CC=CC=N1 YERGTYJYQCLVDM-UHFFFAOYSA-N 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
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- 239000011133 lead Substances 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
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- 229940031993 lithium benzoate Drugs 0.000 description 1
- YNESATAKKCNGOF-UHFFFAOYSA-N lithium bis(trimethylsilyl)amide Chemical compound [Li+].C[Si](C)(C)[N-][Si](C)(C)C YNESATAKKCNGOF-UHFFFAOYSA-N 0.000 description 1
- LDJNSLOKTFFLSL-UHFFFAOYSA-M lithium;benzoate Chemical compound [Li+].[O-]C(=O)C1=CC=CC=C1 LDJNSLOKTFFLSL-UHFFFAOYSA-M 0.000 description 1
- SKEDXQSRJSUMRP-UHFFFAOYSA-N lithium;quinolin-8-ol Chemical compound [Li].C1=CN=C2C(O)=CC=CC2=C1 SKEDXQSRJSUMRP-UHFFFAOYSA-N 0.000 description 1
- 239000006210 lotion Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- SJCKRGFTWFGHGZ-UHFFFAOYSA-N magnesium silver Chemical compound [Mg].[Ag] SJCKRGFTWFGHGZ-UHFFFAOYSA-N 0.000 description 1
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- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
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- 125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
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- YPJRZWDWVBNDIW-MBALSZOMSA-N n,n-diphenyl-4-[(e)-2-[4-[4-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]phenyl]phenyl]ethenyl]aniline Chemical group C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1)=CC=C1C(C=C1)=CC=C1\C=C\C(C=C1)=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 YPJRZWDWVBNDIW-MBALSZOMSA-N 0.000 description 1
- NJWJVPXCXKIBJD-QURGRASLSA-N n,n-diphenyl-6-[(e)-2-[4-(n-phenylanilino)phenyl]ethenyl]naphthalen-2-amine Chemical compound C=1C=C(N(C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1/C=C/C(C=C1C=C2)=CC=C1C=C2N(C=1C=CC=CC=1)C1=CC=CC=C1 NJWJVPXCXKIBJD-QURGRASLSA-N 0.000 description 1
- CLTPAQDLCMKBIS-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-1-ylamino)phenyl]phenyl]-n-naphthalen-1-ylnaphthalen-1-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)C=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 CLTPAQDLCMKBIS-UHFFFAOYSA-N 0.000 description 1
- QKCGXXHCELUCKW-UHFFFAOYSA-N n-[4-[4-(dinaphthalen-2-ylamino)phenyl]phenyl]-n-naphthalen-2-ylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C=C4C=CC=CC4=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=C21 QKCGXXHCELUCKW-UHFFFAOYSA-N 0.000 description 1
- BLFVVZKSHYCRDR-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-2-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-2-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C=CC=CC2=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C=CC=CC3=CC=2)C=C1 BLFVVZKSHYCRDR-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- RYZPDEZIQWOVPJ-UHFFFAOYSA-N n-naphthalen-1-yl-n-[4-[4-[naphthalen-1-yl(naphthalen-2-yl)amino]phenyl]phenyl]naphthalen-2-amine Chemical compound C1=CC=C2C(N(C=3C=CC(=CC=3)C=3C=CC(=CC=3)N(C=3C=C4C=CC=CC4=CC=3)C=3C4=CC=CC=C4C=CC=3)C3=CC4=CC=CC=C4C=C3)=CC=CC2=C1 RYZPDEZIQWOVPJ-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229910052758 niobium Inorganic materials 0.000 description 1
- 239000010955 niobium Substances 0.000 description 1
- GUCVJGMIXFAOAE-UHFFFAOYSA-N niobium atom Chemical compound [Nb] GUCVJGMIXFAOAE-UHFFFAOYSA-N 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- WSGCRAOTEDLMFQ-UHFFFAOYSA-N nonan-5-one Chemical compound CCCCC(=O)CCCC WSGCRAOTEDLMFQ-UHFFFAOYSA-N 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229960003540 oxyquinoline Drugs 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- PIBWKRNGBLPSSY-UHFFFAOYSA-L palladium(II) chloride Chemical compound Cl[Pd]Cl PIBWKRNGBLPSSY-UHFFFAOYSA-L 0.000 description 1
- MXQOYLRVSVOCQT-UHFFFAOYSA-N palladium;tritert-butylphosphane Chemical compound [Pd].CC(C)(C)P(C(C)(C)C)C(C)(C)C.CC(C)(C)P(C(C)(C)C)C(C)(C)C MXQOYLRVSVOCQT-UHFFFAOYSA-N 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- OBCUTHMOOONNBS-UHFFFAOYSA-N phosphorus pentafluoride Chemical compound FP(F)(F)(F)F OBCUTHMOOONNBS-UHFFFAOYSA-N 0.000 description 1
- 238000009832 plasma treatment Methods 0.000 description 1
- HRGDZIGMBDGFTC-UHFFFAOYSA-N platinum(2+) Chemical compound [Pt+2] HRGDZIGMBDGFTC-UHFFFAOYSA-N 0.000 description 1
- 229920001467 poly(styrenesulfonates) Polymers 0.000 description 1
- 229920000172 poly(styrenesulfonic acid) Polymers 0.000 description 1
- 229920000767 polyaniline Polymers 0.000 description 1
- 229920002098 polyfluorene Polymers 0.000 description 1
- 229940005642 polystyrene sulfonic acid Drugs 0.000 description 1
- 229920000123 polythiophene Polymers 0.000 description 1
- RKCAIXNGYQCCAL-UHFFFAOYSA-N porphin Chemical compound N1C(C=C2N=C(C=C3NC(=C4)C=C3)C=C2)=CC=C1C=C1C=CC4=N1 RKCAIXNGYQCCAL-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 238000001226 reprecipitation Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229910052701 rubidium Inorganic materials 0.000 description 1
- IGLNJRXAVVLDKE-UHFFFAOYSA-N rubidium atom Chemical compound [Rb] IGLNJRXAVVLDKE-UHFFFAOYSA-N 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000005055 short column chromatography Methods 0.000 description 1
- PUZPDOWCWNUUKD-UHFFFAOYSA-M sodium fluoride Chemical compound [F-].[Na+] PUZPDOWCWNUUKD-UHFFFAOYSA-M 0.000 description 1
- 125000003003 spiro group Chemical group 0.000 description 1
- FVRNDBHWWSPNOM-UHFFFAOYSA-L strontium fluoride Chemical compound [F-].[F-].[Sr+2] FVRNDBHWWSPNOM-UHFFFAOYSA-L 0.000 description 1
- 229910001637 strontium fluoride Inorganic materials 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052715 tantalum Inorganic materials 0.000 description 1
- GUVRBAGPIYLISA-UHFFFAOYSA-N tantalum atom Chemical compound [Ta] GUVRBAGPIYLISA-UHFFFAOYSA-N 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- PCCVSPMFGIFTHU-UHFFFAOYSA-N tetracyanoquinodimethane Chemical compound N#CC(C#N)=C1C=CC(=C(C#N)C#N)C=C1 PCCVSPMFGIFTHU-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 150000003577 thiophenes Chemical class 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 125000005259 triarylamine group Chemical group 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000005951 trifluoromethanesulfonyloxy group Chemical group 0.000 description 1
- 125000005580 triphenylene group Chemical group 0.000 description 1
- CMPGARWFYBADJI-UHFFFAOYSA-L tungstic acid Chemical compound O[W](O)(=O)=O CMPGARWFYBADJI-UHFFFAOYSA-L 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- HTPBWAPZAJWXKY-UHFFFAOYSA-L zinc;quinolin-8-olate Chemical compound [Zn+2].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 HTPBWAPZAJWXKY-UHFFFAOYSA-L 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/04—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups
- C07C209/06—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms
- C07C209/10—Preparation of compounds containing amino groups bound to a carbon skeleton by substitution of functional groups by amino groups by substitution of halogen atoms with formation of amino groups bound to carbon atoms of six-membered aromatic rings or from amines having nitrogen atoms bound to carbon atoms of six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/58—Naphthylamines; N-substituted derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/57—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton
- C07C211/61—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems of the carbon skeleton with at least one of the condensed ring systems formed by three or more rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
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- C07C2603/00—Systems containing at least three condensed rings
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Description
本發明係關於苯胺衍生物、電荷輸送性清漆及有機電致發光(以下、稱有機EL)元件。
有機EL元件中,作為發光層或電荷注入層可使用由有機化合物所構成的電荷輸送性薄膜。尤其,電洞注入層具有擔負陽極與電洞輸送層或者發光層的電荷之授受,且達成有機EL元件的低電壓驅動及高亮度之重要機能。
電洞注入層之形成方法,大抵分為以蒸鍍法為代表的乾製程與以旋轉塗佈法為代表的濕製程,比較此等各製程,濕製程可大面積有效率地製造平坦性高的薄膜。因此在有機EL顯示器大面積化不斷進展的現在,期望可以濕製程形成之電洞注入層。
有鑑於如此,本發明者們開發了能得到可適用各種濕製程,同時適用於有機EL元件的電洞注入層的場合,可實現優異的EL元件特性之薄膜之電荷輸送性材料或對用於其之有機溶劑溶解性良好的化合物(例如專利
文獻1~4作為參考)。
[專利文獻1]國際公開第2008/032616號
[專利文獻2]國際公開第2008/129947號
[專利文獻3]國際公開第2006/025342號
[專利文獻4]國際公開第2010/058777號
本發明以提供與目前開發的上述專利文獻之技術相同地,顯示對有機溶劑之良好的溶解性,同時進行薄膜化後適用在電洞注入層的場合,可實現具有優異的電特性之有機EL元件的新穎苯胺衍生物、含該苯胺衍生物的電荷輸送性清漆、及有機EL元件為目的。
本發明者們為了達成上述目的,努力研究之結果,發現特定的苯胺衍生物顯示對有機溶劑之高溶解性,同時由使其與摻雜劑一同溶於有機溶劑所調製的清漆得到的薄膜具有高的電荷輸送性,使該薄膜用於有機EL元件的電洞注入層的場合可實現優異的電特性,完成本發
明。
亦即,本發明提供下述苯胺衍生物、電荷輸送性清漆及有機EL元件。
1、一種苯胺衍生物,其特徵係以式(1)表示,
(式中,R1為以Z1取代亦可的碳數1~20之烷基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基、以Z2取代亦可的碳數2~20之雜芳基或式(2)所表示之基,
R2~R55各自獨立,表示氫原子、鹵素原子、硝基、氰基、醛基、羥基、硫醇基、羧酸基、以Z1取代亦可的碳數1~20之烷基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基、以Z2取代亦可的碳數2~20之雜芳基、-C(O)Y1基、-OY2基、-SY3基、-C(O)OY4基、-OC(O)Y5基、-C(O)NHY6基或-C(O)NY7Y8基,
Y1~Y8各自獨立,表示以Z1取代亦可的碳數1~20之烷基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基或以Z2取代亦可的碳數2~20之雜芳基,Z1為鹵素原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、羧酸基、以Z3取代亦可的碳數6~20之芳基或以Z3取代亦可的碳數2~20之雜芳基,Z2為鹵素原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基、羧酸基、以Z3取代亦可的碳數1~20之烷基、以Z3取代亦可的碳數2~20之烯基或以Z3取代亦可的碳數2~20之炔基,Z3為鹵素原子、硝基、氰基、醛基、羥基、硫醇基、磺酸基或羧酸基)。
2、如請求項1記載之苯胺衍生物,其中,R2~R37為氫原子、鹵素原子、以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或-OY2基。
3、如請求項1或2記載之苯胺衍生物,其中,R1為以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或式(2)所表示之基。
4、如請求項3記載之苯胺衍生物,其中,R1為式(2)所表示之基。
5、如請求項4記載之苯胺衍生物,其中,R38~R55為氫原子、鹵素原子、以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或-OY2基。
6、一種電荷輸送性物質,其特徵係由請求項1~5之任1項記載之苯胺衍生物所構成。
7、一種電荷輸送性清漆,其特徵係含有請求項1~5之任1項記載之苯胺衍生物、摻雜劑及有機溶劑。
8、一種電荷輸送性薄膜,其特徵係使用請求項7記載的電荷輸送性清漆來製作。
9、一種電荷輸送性薄膜,其特徵係含有請求項1~5之任1項記載之苯胺衍生物。
10、一種電子裝置,其特徵係具備至少1層請求項8或9記載的電荷輸送性薄膜。
11、一種有機電致發光元件,其特徵係具備至少1層請求項8或9記載的電荷輸送性薄膜。
12、如請求項11記載之有機電致發光元件,其中,前述電荷輸送性薄膜為電洞注入層或電洞輸送層。
13、一種請求項1記載之苯胺衍生物之製造方法,其特徵係使式(3)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物在觸媒存在下進行反應,
(式中,R1~R37同上述。X為鹵素原子或擬鹵素基。)
14、一種請求項1記載之苯胺衍生物之製造方法,其
特徵係使式(6)所表示之胺化合物與式(7)所表示之胺化合物與式(8)所表示之胺化合物在觸媒存在下進行反應,
(式中,R1~R37同上述。X為鹵素原子或擬鹵素基)。
15、一種請求項4記載之苯胺衍生物之製造方法,其特徵係使式(9)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物與式(10)所表示之胺化合物在觸媒存在下進行反應,
(式中,R1~R55同上述。X為鹵素原子或擬鹵素基)。
本發明的苯胺衍生物易溶於有機溶劑,使其與摻雜劑一同溶於有機溶劑,可容易地調製電荷輸送性清漆。
由本發明的電荷輸送性清漆製作的薄膜,因顯示高電荷輸送性,宜用於以有機EL元件為代表之電子裝置用薄
膜。尤其,藉由將該薄膜用在有機EL元件的電洞注入層,可得到電特性優異的有機EL元件。
又,本發明的電荷輸送性清漆,即使在使用旋轉塗佈法或狹縫塗佈法等可大面積成膜的各種濕製程的場合,可再現性佳地製造電荷輸送性優異的薄膜,故可充分對應近年有機EL元件領域之進展。
[實施發明之最佳形態]
[苯胺衍生物]
本發明之苯胺衍生物以式(1)所表示。
式中,R1為以Z1取代亦可的碳數1~20之烷
基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基、以Z2取代亦可的碳數2~20之雜芳基或式(2)所表示之基。
R2~R55各自獨立,表示氫原子、鹵素原子、
硝基、氰基、醛基、羥基、硫醇基、羧酸基、以Z1取代亦可的碳數1~20之烷基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基、以Z2取代亦可的碳數2~20之雜芳基、-C(O)Y1基、-OY2基、-SY3基、-C(O)OY4基、-OC(O)Y5基、-C(O)NHY6基或-C(O)NY7Y8基。
Y1~Y8各自獨立,表示以Z1取代亦可的碳數
1~20之烷基、以Z1取代亦可的碳數2~20之烯基、以Z1取代亦可的碳數2~20之炔基、以Z2取代亦可的碳數6~20之芳基或以Z2取代亦可的碳數2~20之雜芳基。
Z1為鹵素原子、硝基、氰基、醛基、羥基、硫
醇基、磺酸基、羧酸基、以Z3取代亦可的碳數6~20之芳基或以Z3取代亦可的碳數2~20之雜芳基。
Z2為鹵素原子、硝基、氰基、醛基、羥基、硫
醇基、磺酸基、羧酸基、以Z3取代亦可的碳數1~20之烷基、以Z3取代亦可的碳數2~20之烯基或以Z3取代亦可的碳數2~20之炔基。
Z3為鹵素原子、硝基、氰基、醛基、羥基、硫
醇基、磺酸基或羧酸基。
鹵素原子,具體上,可舉例如氟、氯、溴、
碘原子。
碳數1~20之烷基可為直鏈狀、分支狀、環
狀的任一。烷基的具體例,可舉例如甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、t-丁基、n-戊基、n-己基、n-庚基、n-辛基、n-壬基、n-癸基等的碳數1~20之直鏈或分支鏈狀烷基;環丙基、環丁基、環戊基、環己基、環庚基、環辛基、環壬基、環癸基、雙環丁基、雙環戊基、雙環己基、雙環庚基、雙環辛基、雙環壬基、雙環癸基等的碳數3~20之環狀烷基等。
碳數2~20之烯基可為直鏈狀、分支狀、環
狀的任一。烯基的具體例,可舉例如乙烯基、n-1-丙烯基、n-2-丙烯基、1-甲基乙烯基、n-1-丁烯基、n-2-丁烯基、n-3-丁烯基、2-甲基-1-丙烯基、2-甲基-2-丙烯基、1-乙基乙烯基、1-甲基-1-丙烯基、1-甲基-2-丙烯基、n-1-戊烯基、n-1-癸烯基、n-1-二十烯基等。
碳數2~20之炔基可為直鏈狀、分支狀、環
狀的任一。炔基的具體例,可舉例如乙炔基、n-1-丙炔基、n-2-丙炔基、n-1-丁炔基、n-2-丁炔基、n-3-丁炔基、1-甲基-2-丙炔基、n-1-戊炔基、n-2-戊炔基、n-3-戊炔基、n-4-戊炔基、1-甲基-n-丁炔基、2-甲基-n-丁炔基、3-甲基-n-丁炔基、1,1-二甲基-n-丙炔基、n-1-己炔基、n-1-癸炔基、n-1-十五炔基、n-1-二十炔基等。
烷基、烯基及炔基的碳數以12以下為佳,6
以下更佳,4以下又更佳。
碳數6~20之芳基的具體例,可舉例如苯
基、1-萘基、2-萘基、1-蒽基、2-蒽基、9-蒽基、1-菲基、2-菲基、3-菲基、4-菲基、9-菲基等。
碳數2~20之雜芳基的具體例,可舉例如2-
噻吩基、3-噻吩基、2-呋喃基、3-呋喃基、2-噁唑基、4-噁唑基、5-噁唑基、3-異噁唑基、4-異噁唑基、5-異噁唑基、2-噻唑基、4-噻唑基、5-噻唑基、3-異噻唑基、4-異噻唑基、5-異噻唑基、2-咪唑基、4-咪唑基、2-吡啶基、3-吡啶基、4-吡啶基等。
芳基及雜芳基的碳數以14以下為佳,10以下
更佳,6以下又更佳。
R1方面,以Z1取代亦可的碳數1~20之烷
基、以Z2取代亦可的碳數6~20之芳基或式(2)所表示之基為佳,以Z1取代亦可的碳數1~10之烷基、以Z2取代亦可的苯基或式(2)所表示之基更佳,式(2)所表示之基最佳。
R1為式(2)所表示之基的場合,尤以R38~R55
為氫原子、鹵素原子、以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基、以Z1取代亦可的碳數1~20之烷氧基(Y2為以Z1取代亦可的碳數1~20之烷基之-OY2基)或以Z2取代亦可的碳數6~20之芳基氧基(Y2為以Z2取代亦可的碳數6~20之芳基的-OY2基)為佳,氫原子、氟原子、以Z1取代亦可的碳數1~10之烷
基或以Z2取代亦可的苯基更佳,氫原子、氟原子或以Z2取代亦可的苯基又更佳,氫原子最佳。
又,R2~R37方面,以氫原子、鹵素原子、以
Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基、以Z1取代亦可的碳數1~20之烷氧基或以Z2取代亦可的碳數6~20之芳基氧基為佳,氫原子、氟原子、以Z1取代亦可的碳數1~10之烷基或以Z2取代亦可的苯基更佳,氫原子、氟原子或以Z2取代亦可的苯基又更佳,氫原子最佳。
又,R2~R55及Y1~Y8為烷基、烯基、炔
基、芳基或雜芳基的場合,取代基Z1以鹵素原子或以Z3取代亦可的碳數6~20之芳基為佳,鹵素原子或以Z3取代亦可的苯基更佳,不存在(亦即,為非取代)為最佳。
又,取代基Z2以鹵素原子或以Z3取代亦可的碳數1~20之烷基為佳,鹵素原子或以Z3取代亦可的碳數1~4之烷基更佳,不存在(亦即,為非取代)為最佳。
接著,Z3以鹵素原子為佳,氟更佳,不存在(亦即,為非取代)為最佳。
以下、列舉式(1)所表示之苯胺衍生物的具體
例,但不限於此等。又,式中,「Me」為甲基、「Et」為乙基、「n-Pr」為n-丙基、「i-Pr」為i-丙基、「n-Bu」為n-丁基、「i-Bu」為異丁基、「s-Bu」為s-丁基、「t-Bu」為t-丁基、「n-Pen」為n-戊基、「n-Hex」為n-己基、「n-Hep」為n-庚基、「Ph」為苯基。
[苯胺衍生物之製造方法]
本發明的苯胺衍生物可藉由使式(3)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物在
觸媒存在下進行反應來製造(路徑1)。
(式中,X各自獨立,為鹵素原子或擬鹵素基。R1~R37同上述。)
又,本發明的苯胺衍生物亦可藉由使式(6)所表示之胺化合物與式(7)所表示之胺化合物與式(8)所表示之胺化合物在觸媒存在下進行反應來製造(路徑2)。
(式中,X及R1~R37同上述。)
接著,R1為式(2)所表示之基的本發明的苯胺衍生物(式(1')),可藉由使式(9)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物與式(10)所表示之胺化合物在觸媒存在下進行反應來製造(路徑3)。
(式中,X及R1~R55同上述。)
上述路徑1~3中,X所表示之鹵素原子方面,可舉例如與上述同樣者。又,擬鹵素基方面,可舉例如甲烷磺醯基氧基、三氟甲烷磺醯基氧基、九氟丁烷磺醯基氧基等的(氟)烷基磺醯基氧基;苯磺醯基氧基、甲苯磺醯基氧基等的芳香族磺醯基氧基等。
式(3)所表示之胺化合物的具體例,可舉例如N-甲基-雙(4-胺基苯基)胺、N,N-雙(p-胺基苯基)苯胺等,式(6)所表示之胺化合物的具體例,可舉例如N-甲基-雙(4-溴苯基)胺、N,N-雙(p-溴苯基)苯胺等,式(9)所表示之胺化合物的具體例,可舉例如參(4-胺基苯基)胺等,但皆不限於此等。
式(4)、(5)、(10)所表示之胺化合物的具體
例,可舉例如4'-溴-N-苯基-[1,1'-聯苯基]-4-胺等,式(7)、(8)所表示之胺化合物的具體例,可舉例如N,N-二苯基-p-伸苯基二胺等,但皆不限於此等。
式(3)所表示之胺化合物與式(4)、(5)所表示之
胺化合物的添加比、式(6)所表示之胺化合物與式(7)、(8)所表示之胺化合物的添加比、及式(9)所表示之胺化合物與式(4)、(5)、(10)所表示之胺化合物的添加比以莫耳比計可為1以上,但以1~1.2左右為較佳。
上述反應所使用的觸媒,可舉例如氯化銅、
溴化銅、碘化銅等的銅觸媒;四(三苯基膦)鈀(Pd(PPh3)4)、雙(三苯基膦)二氯鈀(Pd(PPh3)2Cl2)、雙(亞芐基丙酮)鈀(Pd(dba)2)、三(亞芐基丙酮)二鈀(Pd2(dba)3)、雙(三-t-丁基膦)鈀(Pd(P-t-Bu3)2)等的鈀觸媒等。此等之觸媒可1種單獨或2種以上組合使用。又,此等之觸媒可與習知適當的配位子一起使用。
觸媒的使用量,相對式(3)、(6)或(9)所表示之
胺化合物1mol,可為0.001~0.2mol左右,但以0.005~0.05mol左右為較佳。
又,使用配位子的場合,其使用量相對使用的金屬錯合物,可為0.1~5當量,但以1~4當量為較佳。
上述反應可在溶劑中進行。溶劑為不對反應
有負面影響者,則不特別限定。溶劑的具體例,可舉例如脂肪族烴類(戊烷、n-己烷、n-辛烷、n-癸烷、萘烷等)、
鹵素化脂肪族烴類(氯仿、二氯甲烷、二氯乙烷、四氯化碳等)、芳香族烴類(苯、硝基苯、甲苯、o-二甲苯、m-二甲苯、p-二甲苯、三甲苯等)、鹵素化芳香族烴類(氯苯、溴苯、o-二氯苯、m-二氯苯、p-二氯苯等)、醚類(二乙基醚、二異丙基醚、t-丁基甲基醚、四氫呋喃、二噁烷、1,2-二甲氧基乙烷、1,2-二乙氧基乙烷等)、酮類(丙酮、甲基乙基酮、甲基異丁基酮、二-n-丁基酮、環己酮等)、醯胺類(N,N-二甲基甲醯胺、N,N-二甲基乙醯胺等)、內醯胺及內酯類(N-甲基吡咯烷酮、γ-丁內酯等)、尿素類(N,N-二甲基咪唑啉酮、四甲基脲等)、亞碸類(二甲基亞碸、環丁碸等)、腈類(乙腈、丙腈、丁腈等)等。此等之溶劑可1種單獨或2種以上混合使用。
反應溫度在使用溶劑之熔點至沸點為止的範
圍適宜設定即可,尤其,以0~200℃左右為佳,20~150℃更佳。
反應完畢後依據常法進行後處理,可得到目的之苯胺衍生物。
[電荷輸送性清漆]
本發明的電荷輸送性清漆為含有式(1)所表示之苯胺衍生物所構成的電荷輸送性物質與有機溶劑者,但為使電荷輸送能力等提升,因應必要,可含摻雜劑。
摻雜劑方面,為溶於清漆使用之至少1種的溶劑者則不特別限定,無機系摻雜劑、有機系摻雜劑皆可
使用。
無機系摻雜劑方面,可舉例如氯化氫、硫
酸、硝酸、磷酸等的無機酸;氯化鋁(III)(AlCl3)、四氯化鈦(IV)(TiCl4)、三溴化硼(BBr3)、三氟化硼醚錯合物(BF3.OEt2)、氯化鐵(III)(FeCl3)、氯化銅(II)(CuCl2)、五氯化銻(V)(SbCl5)、五氟化銻(V)(SbF5)、五氟化砷(V)(AsF5)、五氟化磷(PF5)、三(4-溴苯基)鋁六氯銻酸(TBPAH)等的金屬鹵素化物;Cl2、Br2、I2、ICl、ICl3、IBr、IF4等的鹵素;磷鉬酸、磷鎢酸等的雜多元酸等。
有機系摻雜劑方面,可舉例如苯磺酸、對甲
苯磺酸、p-苯乙烯磺酸、2-萘磺酸、4-羥基苯磺酸、5-磺基水楊酸、p-十二烷基苯磺酸、二己基苯磺酸、2,5-二己基苯磺酸、二丁基萘磺酸、6,7-二丁基-2-萘磺酸、十二烷基萘磺酸、3-十二烷基-2-萘磺酸、己基萘磺酸、4-己基-1-萘磺酸、辛基萘磺酸、2-辛基-1-萘磺酸、己基萘磺酸、7-己基-1-萘磺酸、6-己基-2-萘磺酸、二壬基萘磺酸、2,7-二壬基-4-萘磺酸、二壬基萘二磺酸、2,7-二壬基-4,5-萘二磺酸、國際公開第2005/000832號記載之1,4-苯並二噁烷二磺酸化合物、國際公開第2006/025342號記載之芳基磺酸化合物、國際公開第2009/096352號記載之芳基磺酸化合物、聚苯乙烯磺酸等的芳基磺酸化合物;10-樟腦磺酸等的非芳基磺酸化合物;7,7,8,8-四氰基對苯二醌二甲烷(TCNQ)、2,3-二氯-5,6-二氰基-1,4-苯醌(DDQ)等的有機氧化劑等。
此等無機系及有機系的摻雜劑可1種單獨或2
種以上組合使用。
此等之摻雜劑中以雜多元酸較佳。藉由作為
摻雜劑使用雜多元酸,可得到不僅來自以銦錫氧化物(ITO)、銦鋅氧化物(IZO)為代表的透明電極的高電洞接受能力,亦顯示來自以鋁為代表的金屬陽極的高電洞接受能力之電荷輸送性優異的薄膜。
雜多元酸係指代表地以式(B1)所表示之
Keggin型或者式(B2)所表示之Dawson型的化學構造表示、且具有雜原子位於分子之中心的構造,由釩(V)、鉬(Mo)、鎢(W)等的含氧酸之異多元酸與異種元素的含氧酸進行縮合而成的多元酸。如此之異種元素的含氧酸方面,主要可舉例如矽(Si)、磷(P)、砷(As)的含氧酸。
雜多元酸的具體例,可舉例如磷鉬酸、矽鉬
酸、磷鎢酸、矽鎢酸、磷鎢鉬酸等。此等可1種單獨或2種以上組合使用。又,本發明使用的雜多元酸可以市售品取得,又,亦可以習知方法合成。
尤其,摻雜劑為1種類之雜多元酸所構成的
場合,該1種類的雜多元酸以磷鎢酸或磷鉬酸為佳,磷鎢
酸更佳。又,摻雜劑為2種類以上的雜多元酸所構成的場合,其2種類以上的雜多元酸中至少1個以磷鎢酸或磷鉬酸為佳,磷鎢酸更佳。
又,雜多元酸在元素分析等的定量分析中,
比一般式所表示之構造之元素的數為多者或少者、其以市售品取得者、或者、依據習知合成方法適當合成者,則在本發明中可使用。
亦即,例如一般磷鎢酸以化學式H3(PW12O40)
.nH2O、磷鉬酸以化學式H3(PMo12O40).nH2O分別表示,但定量分析中,該式中之P(磷)、O(氧)或W(鎢)或者Mo(鉬)的數為多者或少者、其以市售品取得者、或者依據習知合成方法適當合成者,則可在本發明中使用。此時,本發明所規定的雜多元酸之質量非合成物或市售品中純粹的磷鎢酸之質量(磷鎢酸含量),係指可作為市售品取得之形態及習知合成法可單離之形態中,含水合水或其他的雜質等的狀態之全質量。
又,芳基磺酸化合物亦宜使用。尤其以式(11)
或(12)所表示之芳基磺酸化合物為佳。
式(11)中,A1為-O-或-S-,但以-O-為佳。A2
為萘環或蒽環,但以萘環為佳。A3為2~4價之全氟聯苯
基,p為A1與A3之鍵結數,為符合2≦p≦4之整數,但以A3為2價之全氟聯苯基,且P為2為佳。q為鍵結於A2的磺酸基數,為符合1≦q≦4之整數,但以2較佳。
式(12)中,A4~A8各自獨立,表示氫原子、
鹵素原子、氰基、碳數1~20之烷基、碳數1~20之鹵素化烷基或碳數2~20之鹵素化烯基,但A4~A8中至少3個為鹵素原子。r為鍵結於萘環的磺酸基數,為符合1≦r≦4之整數,但以2~4為佳,2更佳。
碳數1~20之鹵素化烷基方面,可舉例如三
氟甲基、2,2,2-三氟乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、1,1,2,2,3,3,3-七氟丙基、4,4,4-三氟丁基、3,3,4,4,4-五氟丁基、2,2,3,3,4,4,4-七氟丁基、1,1,2,2,3,3,4,4,4-九氟丁基等。
碳數2~20之鹵素化烯基方面,可舉例如全氟乙烯基、1-全氟丙烯基、全氟烯丙基、全氟丁烯基等。
其他鹵素原子、碳數1~20之烷基的例方面,可舉例如與上述同樣者,但鹵素原子方面,以氟原子為佳。
此等之中,以A4~A8以氫原子、鹵素原子、氰基、碳數1~10之烷基、碳數1~10之鹵素化烷基或碳數2~10之鹵素化烯基,且A4~A8中至少3個為氟原子為佳。又,為氫原子、氟原子、氰基、碳數1~5之烷基、碳數1~5的氟化烷基或碳數2~5的氟化烯基,且A4~A8中至少3個為氟原子更佳。進而以氫原子、氟原子、氰基、碳數1~5的全氟烷基或碳數1~5的全氟烯
基,且A4、A5及A8為氟原子更佳。
又,全氟烷基係指烷基的氫原子全部被氟原
子取代的基,全氟烯基係指烯基的氫原子全部被氟原子取代的基。
本發明中之其他的摻雜劑,可舉例較佳的芳
基磺酸化合物的具體例,但不限於此等。
本發明的電荷輸送性清漆含摻雜劑之場合,
摻雜劑的使用量考量摻雜劑的種類、所期望的電荷輸送性的程度等適宜決定,故無法一概而論,以質量比計相對本發明的苯胺衍生物所構成的電荷輸送性物質(以下、僅稱為電荷輸送性物質)1,大約為0.01~50左右的範圍內。
尤其,使用雜多元酸作為摻雜劑的場合,藉
由使雜多元酸,以質量比計相對電荷輸送性物質1而言,
為0.5~30.0左右、較佳為1.0~20.0左右、更佳為2.0~15.0左右、又更佳為3.0~12.0左右、再更佳為4.0~11.0左右,可再現性佳地得到使用於有機EL元件場合賦予高亮度之電荷輸送性薄膜。
另一方面,作為摻雜劑使用芳基磺酸化合物
的場合,藉由使芳基磺酸化合物以莫耳比計相對電荷輸送性物質1而言,為0.05~15.0、較佳為0.10~10.0、更佳為0.25~7.0、又更佳為0.50~5.0、再更佳為0.75~3.0,可再現性佳地得到使用於有機EL元件場合賦予高亮度之電荷輸送性薄膜。
進而,本發明的電荷輸送性清漆可含有機矽
烷化合物。藉由含有有機矽烷,可使對以與電洞注入層相接之方式於與電洞輸送層或發光層之所謂陽極相反側層合的層之電洞注入能力提高,結果,可實現更高電特性。
該有機矽烷化合物,可舉例如二烷氧基矽烷
化合物、三烷氧基矽烷化合物或四烷氧基矽烷化合物。此等可1種單獨或2種以上組合使用。
尤其有機矽烷化合物方面,以二烷氧基矽烷
化合物或三烷氧基矽烷化合物為佳,三烷氧基矽烷化合物更佳。
二烷氧基矽烷化合物、三烷氧基矽烷化合物
及四烷氧基矽烷化合物,可舉例如式(13)~(15)所表示之者。
SiR’2(OR)2 (13)
SiR’(OR)3 (14)
Si(OR)4 (15)
式中,R各自獨立,表示以Z4取代亦可的碳數1~20之烷基、以Z4取代亦可的碳數2~20之烯基、以Z4取代亦可的碳數2~20之炔基、以Z5取代亦可的碳數6~20之芳基或以Z5取代亦可的碳數2~20之雜芳基。R'各自獨立,表示以Z6取代亦可的碳數1~20之烷基、以Z6取代亦可的碳數2~20之烯基、以Z6取代亦可的碳數2~20之炔基、以Z7取代亦可的碳數6~20之芳基或以Z7取代亦可的碳數2~20之雜芳基。
Z4為鹵素原子、以Z8取代亦可的碳數6~20之芳基或以Z8取代亦可的碳數2~20之雜芳基。
Z5為鹵素原子、以Z8取代亦可的碳數1~20之烷基、以Z8取代亦可的碳數2~20之烯基或以Z8取代亦可的碳數2~20之炔基。
Z6為鹵素原子、以Z8取代亦可的碳數6~20之芳基、以Z8取代亦可的碳數2~20之雜芳基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇基、異氰酸酯基(-NCO)、胺基、-NHY9基或-NY10Y11基。
Z7為鹵素原子、以Z8取代亦可的碳數1~20之烷基、以Z8取代亦可的碳數2~20之烯基、以Z8取代亦可的碳數2~20之炔基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基(-NHCONH2)、硫醇
基、異氰酸酯基(-NCO)、胺基、-NHY9基或-NY10Y11基。
Y9~Y11各自獨立,表示以Z8取代亦可的碳數
1~20之烷基、以Z8取代亦可的碳數2~20之烯基、以Z8取代亦可的碳數2~20之炔基、以Z8取代亦可的碳數6~20之芳基或以Z8取代亦可的碳數2~20之雜芳基。
Z8為鹵素原子、胺基、硝基、氰基或硫醇基。
式(13)~(15)中鹵素原子、碳數1~20之烷基、碳數2~20之烯基、碳數2~20之炔基、碳數6~20之芳基、及碳數2~20之雜芳基方面,可舉例如與上述同樣者。
R及R'中,烷基、烯基及炔基的碳數較佳為10以下,更佳為6以下,又更佳為4以下。又,芳基及雜芳基的碳數較佳為14以下,更佳為10以下,又更佳為6以下。
R方面,以Z4取代亦可的碳數1~20之烷基、碳數2~20之烯基或以Z5取代亦可的碳數6~20之芳基為佳,以Z4取代亦可的碳數1~6之烷基、碳數2~6的烯基或以Z5取代亦可的苯基更佳,以Z4取代亦可的碳數1~4之烷基或以Z5取代亦可的苯基又更佳,以Z4取代亦可的甲基或乙基再更佳。
又,R'方面,以Z6取代亦可的碳數1~20之烷基或以Z7取代亦可的碳數6~20之芳基為佳,以Z6取代亦可的碳數1~10之烷基或以Z7取代亦可的碳數6~14之芳基更佳,以Z6取代亦可的碳數1~6之烷基或以Z7
取代亦可的碳數6~10之芳基又更佳,以Z6取代亦可的碳數1~4之烷基或以Z7取代亦可的苯基再更佳。
又,複數的R全部可相同或相異、複數的R'
全部亦可相同或相異。
Z4方面,以鹵素原子或以Z8取代亦可的碳數
6~20之芳基為佳,氟原子或以Z8取代亦可的苯基更佳,不存在(亦即,為非取代)為最佳。
又,Z5方面,以鹵素原子或以Z8取代亦可的
碳數6~20之烷基為佳,氟原子或以Z8取代亦可的碳數1~10之烷基更佳,不存在(亦即,為非取代)為最佳。
另一方面,Z6方面,以鹵素原子、以Z8取代
亦可的苯基、以Z8取代亦可的呋喃基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、以Z8取代亦可的苯基胺基或以Z8取代亦可的二苯基胺基為佳,鹵素原子更佳,氟原子或不存在(亦即,為非取代)又更佳。
又,Z7方面,以鹵素原子、以Z8取代亦可的
碳數1~20之烷基、以Z8取代亦可的呋喃基、環氧基環己基、環氧丙氧基、甲基丙烯醯氧基、丙烯醯氧基、脲基、硫醇基、異氰酸酯基、胺基、以Z8取代亦可的苯基胺基或以Z8取代亦可的二苯基胺基為佳,鹵素原子更佳,氟原子或不存在(亦即,為非取代)又更佳。
接著,Z8方面,以鹵素原子為佳,氟原子或
不存在(亦即,為非取代)更佳。
以下,列舉本發明可使用的有機矽烷化合物
的具體例,但不限於此等。
二烷氧基矽烷化合物的具體例,可舉例如二甲基二甲氧基矽烷、二甲基二乙氧基矽烷、甲基乙基二甲氧基矽烷、二乙基二甲氧基矽烷、二乙基二乙氧基矽烷、甲基丙基二甲氧基矽烷、甲基丙基二乙氧基矽烷、二異丙基二甲氧基矽烷、苯基甲基二甲氧基矽烷、乙烯基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二甲氧基矽烷、3-環氧丙氧基丙基甲基二乙氧基矽烷、3-(3,4-環氧基環己基)乙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二甲氧基矽烷、3-甲基丙烯醯氧基丙基甲基二乙氧基矽烷、3-巰基丙基甲基二甲氧基矽烷、γ-胺基丙基甲基二乙氧基矽烷、N-(2-胺基乙基)胺基丙基甲基二甲氧基矽烷、3,3,3-三氟丙基甲基二甲氧基矽烷等。
三烷氧基矽烷化合物的具體例,可舉例如甲
基三甲氧基矽烷、甲基三乙氧基矽烷、乙基三甲氧基矽烷、乙基三乙氧基矽烷、丙基三甲氧基矽烷、丙基三乙氧基矽烷、丁基三甲氧基矽烷、丁基三乙氧基矽烷、戊基三甲氧基矽烷、戊基三乙氧基矽烷、庚基三甲氧基矽烷、庚基三乙氧基矽烷、辛基三甲氧基矽烷、辛基三乙氧基矽烷、十二烷基三甲氧基矽烷、十二烷基三乙氧基矽烷、十六基三甲氧基矽烷、十六基三乙氧基矽烷、十八烷基三甲氧基矽烷、十八烷基三乙氧基矽烷、苯基三甲氧基矽烷、苯基三乙氧基矽烷、乙烯基三甲氧基矽烷、乙烯基三乙氧
基矽烷、γ-胺基丙基三甲氧基矽烷、3-胺基丙基三乙氧基矽烷、γ-環氧丙氧基丙基三甲氧基矽烷、3-環氧丙氧基丙基三乙氧基矽烷、γ-甲基丙烯醯氧基丙基三甲氧基矽烷、γ-甲基丙烯醯氧基丙基三乙氧基矽烷、三乙氧基(4-(三氟甲基)苯基)矽烷、十二烷基三乙氧基矽烷、3,3,3-三氟丙基三甲氧基矽烷、(三乙氧基矽烷基)環己烷、全氟辛基乙基三乙氧基矽烷、三乙氧基氟矽烷、十三氟-1,1,2,2-四氫辛基三乙氧基矽烷、五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷、3-(七氟異丙氧基)丙基三乙氧基矽烷、十七氟-1,1,2,2-四氫癸基三乙氧基矽烷、三乙氧基-2-噻吩基矽烷、3-(三乙氧基矽烷基)呋喃等。
四烷氧基矽烷化合物的具體例,可舉例如四
甲氧基矽烷、四乙氧基矽烷、四丙氧基矽烷等。
此等之中,以3,3,3-三氟丙基甲基二甲氧基矽
烷、三乙氧基(4-(三氟甲基)苯基)矽烷、3,3,3-三氟丙基三甲氧基矽烷、全氟辛基乙基三乙氧基矽烷或五氟苯基三甲氧基矽烷、五氟苯基三乙氧基矽烷為佳。
本發明的電荷輸送性清漆包含有機矽烷化合
物之場合,其含量若考量維持得到的薄膜之高電荷輸送性之點,相對電荷輸送性物質及摻雜劑的總質量,通常為0.1~50質量%左右,但若考量抑制得到的薄膜之電荷輸送性的降低且使對以與電洞注入層相接之方式層合於電洞輸送層或發光層之所謂陽極的相反側之層的電洞注入能力提高,較佳為0.5~40質量%左右、更佳為0.8~30質量%
左右、又更佳為1~20質量%左右。
又,本發明的電荷輸送性清漆中,除上述苯
胺衍生物所構成的電荷輸送性物質外,亦可使用習知其他的電荷輸送性物質。
作為調製電荷輸送性清漆時所使用的有機溶
劑,可使用能使電荷輸送性物質及摻雜劑良好溶解的高溶解性溶劑。
如此之高溶解性溶劑,可使用例如N,N-二甲
基甲醯胺、N,N-二甲基乙醯胺、N-甲基吡咯烷酮、1,3-二甲基-2-咪唑啉酮、二乙二醇單甲基醚等的有機溶劑。此等之溶劑可1種單獨或2種以上混合使用,其使用量相對清漆使用之溶劑全體,可為5~100質量%。
又,電荷輸送性物質及摻雜劑以皆於上述溶
劑完全溶解、或成為均勻分散狀態為佳,以完全溶解更佳。
又,本發明中,藉由清漆中含有至少1種在
25℃具有10~200mPa.s、尤其35~150mPa.s之黏度且在常壓(大氣壓)沸點50~300℃、尤其150~250℃之高黏度有機溶劑,清漆之黏度的調整變得容易,結果,可再現性佳地得到平坦性高的薄膜、可因應使用的塗佈方法調整清漆。
作為高黏度有機溶劑,非特別限定者,可舉
例如環己醇、乙二醇、乙二醇二縮水甘油基醚、1,3-辛二醇、二乙二醇、二丙二醇、三乙二醇、三丙二醇、1,3-丁
烷二醇、2,3-丁烷二醇、1,4-丁烷二醇、丙二醇、伸己基二醇等。此等之溶劑可1種單獨或2種以上混合使用。
相對於本發明的清漆所使用的溶劑全體之高
黏度有機溶劑之添加比例,以固體不析出的範圍內為佳,在固體不析出的範圍下,添加比例以5~80質量%為佳。
進而,以對基板之濕潤性的提升、溶劑之表
面張力的調整、極性的調整、沸點的調整等的目的,相對清漆使用之溶劑全體,可以較佳為1~90質量%、更佳為1~50質量%的比例混合其他的溶劑。
如此之溶劑,可舉例如丙二醇單甲基醚、乙
二醇單丁基醚、二乙二醇二乙基醚、二乙二醇二甲基醚、二乙二醇單乙基醚乙酸酯、二乙二醇單丁基醚乙酸酯、二丙二醇單甲基醚、丙二醇單甲基醚乙酸酯、二乙二醇單乙基醚、二丙酮醇、γ-丁內酯、乙基乳酸酯、n-己基乙酸酯等,但不限於此等。此等之溶劑可1種單獨或2種以上混合使用。
本發明的清漆之黏度為因應製作的薄膜之厚
度等或固形分濃度適宜設定者,但通常在25℃為1~50mPa.s。
又,本發明中之電荷輸送性清漆之固形分濃
度,為考量清漆之黏度及表面張力等或製作的薄膜之厚度等而適宜設定者,但通常為0.1~10.0質量%左右,若考量提升清漆之塗佈性,較佳為0.5~5.0質量%、更佳為1.0~3.0質量%。
藉由使上述電荷輸送性清漆於基材上塗佈後
燒成,可於基材上形成電荷輸送性薄膜。
清漆之塗佈方法方面,非特別限定者,可舉
例如浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈、噴墨法、噴霧法、狹縫塗佈法等,以因應塗佈方法調整清漆之黏度及表面張力為佳。
又,使用本發明的清漆的場合,燒成環境亦
非特別限定者,不僅大氣環境、在氮等的惰性氣體或真空中亦可得到具有均勻的成膜面及高電荷輸送性之薄膜。
燒成溫度為考量得到的薄膜之用途、賦予得
到的薄膜之電荷輸送性的程度等,在100~260℃左右的範圍內適宜設定者,但將得到的薄膜作為有機EL元件的電洞注入層的場合,以140~250℃左右為佳,145~240℃左右更佳。
又,燒成時以表現更高的均勻成膜性、在基
材上使反應進行之目的,亦可設置2階段以上的溫度變化。加熱使用例如加熱板或烤箱等適當的機器進行即可。
電荷輸送性薄膜之膜厚,雖不特別限定,在
有機EL元件內用作為電洞注入層的場合,以5~200nm為佳。改變膜厚之方法方面,有使清漆中之固形分濃度改變、使塗佈時之基板上的溶液量改變等的方法。
[有機EL元件]
使用本發明的電荷輸送性清漆,製作OLED元件場合
的使用材料或製作方法方面,可舉例如下述般者,但不限於此等。
使用的電極基板,以預先進行洗劑、醇、純
水等之液體洗淨進行淨化為佳,例如在陽極基板以使用前進行UV臭氧處理、氧-電漿處理等的表面處理為佳。但陽極材料以有機物為主成分之場合,可不進行表面處理。
具有由本發明的電荷輸送性清漆得到的薄膜
所構成的電洞注入層之OLED元件的製作方法例如以下。
藉由上述方法,於陽極基板上塗佈本發明的
電荷輸送性清漆進行燒成,於電極上製作電洞注入層。將其導入真空蒸鍍裝置內,依序蒸鍍電洞輸送層、發光層、電子輸送層、電子輸送層/電洞阻隔層、陰極金屬,作成OLED元件。又,因應必要,可於發光層與電洞輸送層間設置電子阻隔層。
陽極材料方面,可舉例如由以銦錫氧化物
(ITO)、銦鋅氧化物(IZO)為代表的透明電極或鋁為代表的金屬或此等之合金等所構成的金屬陽極,以經平坦化處理者為佳。亦可使用具有高電荷輸送性的聚噻吩衍生物或聚苯胺衍生物。
又,構成金屬陽極的其他的金屬方面,可舉
例如鈧、鈦、釩、鉻、錳、鐵、鈷、鎳、銅、鋅、鎵、釔、鋯、鈮、鉬、釕、銠、鈀、鎘、銦、鈧、鑭、鈰、鐠、釹、鉅、釤、銪、釓、鋱、鏑、鈥、鉺、銩、鐿、鉿、鉈、鎢、錸、鋨、銥、鉑、金、鈦、鉛、鉍或此等之
合金等,但不限於此等。
形成電洞輸送層的材料方面,可舉例如(三苯
基胺)二聚物衍生物、[(三苯基胺)二聚物]螺二聚物、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-聯苯胺(α-NPD)、N,N'-雙(萘-2-基)-N,N'-雙(苯基)-聯苯胺、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-聯苯胺、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-螺二芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-螺二芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二甲基-芴、N,N'-雙(3-甲基苯基)-N,N'-雙(苯基)-9,9-二苯基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-9,9-二苯基-芴、N,N'-雙(萘-1-基)-N,N'-雙(苯基)-2,2'-二甲基聯苯胺、2,2',7,7'-四(N,N-二苯基胺基)-9,9-螺二芴、9,9-雙[4-(N,N-雙-聯苯基-4-基-胺基)苯基]-9H-芴、9,9-雙[4-(N,N-雙-萘-2-基-胺基)苯基]-9H-芴、9,9-雙[4-(N-萘-1-基-N-苯基胺基)-苯基]-9H-芴、2,2',7,7'-四[N-萘基(苯基)-胺基]-9,9-螺二芴、N,N'-雙(菲-9-基)-N,N'-雙(苯基)-聯苯胺、2,2'-雙[N,N-雙(聯苯基-4-基)胺基]-9,9-螺二芴、2,2'-雙(N,N-二苯基胺基)-9,9-螺二芴、二-[4-(N,N-二(p-甲苯基)胺基)-苯基]環己烷、2,2',7,7'-四(N,N-二(p-甲苯基))胺基-9,9-螺二芴、N,N,N',N'-四-萘-2-基-聯苯胺、N,N,N',N'-四-(3-甲基苯基)-3,3'-二甲基聯苯胺、N,N'-二(萘基)-N,N'-二(萘-2-基)-聯苯胺、N,N,N',N'-四(萘基)-聯苯胺、N,N'-二(萘-2-基)-N,N'-二苯基聯苯胺-1,4-二胺、N1,N4-二苯基-N1,N4-二(m-
甲苯基)苯-1,4-二胺、N2,N2,N6,N6-四苯基萘-2,6-二胺、三(4-(喹啉-8-基)苯基)胺、2,2'-雙(3-(N,N-二(p-甲苯基)胺基)苯基)聯苯、4,4',4"-三[3-甲基苯基(苯基)胺基]三苯基胺(m-MTDATA)、4,4',4"-三[1-萘基(苯基)胺基]三苯基胺(1-TNATA)等的三芳基胺類、5,5"-雙-{4-[雙(4-甲基苯基)胺基]苯基}-2,2':5',2"-三聯噻吩(BMA-3T)等的寡聚噻吩類等。
形成發光層的材料方面,可舉例如三(8-羥基
喹啉)鋁(III)(Alq3)、雙(8-羥基喹啉)鋅(II)(Znq2)、雙(2-甲基-8-羥基喹啉)(p-苯基酚鹽)鋁(III)(BAlq)、4,4'-雙(2,2-二苯基乙烯基)聯苯、9,10-二(萘-2-基)蒽、2-t-丁基-9,10-二(萘-2-基)蒽、2,7-雙[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2-甲基-9,10-雙(萘-2-基)蒽、2-(9,9-螺二芴-2-基)-9,9-螺二芴、2,7-雙(9,9-螺二芴-2-基)-9,9-螺二芴、2-[9,9-二(4-甲基苯基)-芴-2-基]-9,9-二(4-甲基苯基)芴、2,2'-二芘基-9,9-螺二芴、1,3,5-三(芘-1-基)苯、9,9-雙[4-(芘基)苯基]-9H-芴、2,2'-二(9,10-二苯基蒽)、2,7-二芘基-9,9-螺二芴、1,4-二(芘-1-基)苯、1,3-二(芘-1-基)苯、6,13-二(聯苯基-4-基)五環素、3,9-二(萘-2-基)苝、3,10-二(萘-2-基)苝、三[4-(芘基)-苯基]胺、10,10'-二(聯苯基-4-基)-9,9'-二蒽、N,N'-二(萘-1-基)-N,N'-二苯基-[1,1':4',1":4",1'''-四聯苯基]-4,4'''-二胺、4,4'-二[10-(萘-1-基)蒽-9-基]聯苯、二苯並{[F,F']-4,4',7,7'-四苯基}二茚并[1,2,3-cd:1',2',3'-lm]苝、1-(7-(9,9'-二蒽-10-基)-9,9-二甲
基-9H-芴-2-基)芘、1-(7-(9,9'-二蒽-10-基)-9,9-二己基-9H-芴-2-基)芘、1,3-雙(咔唑-9-基)苯、1,3,5-三(咔唑-9-基)苯、4,4',4"-三(咔唑-9-基)三苯基胺、4,4'-雙(咔唑-9-基)聯苯基(CBP)、4,4'-雙(咔唑-9-基)-2,2'-二甲基聯苯、2,7-雙(咔唑-9-基)-9,9-二甲基芴、2,2',7,7'-四(咔唑-9-基)-9,9-螺二芴、2,7-雙(咔唑-9-基)-9,9-二(p-甲苯基)芴、9,9-雙[4-(咔唑-9-基)-苯基]芴、2,7-雙(咔唑-9-基)-9,9-螺二芴、1,4-雙(三苯基矽烷基)苯、1,3-雙(三苯基矽烷基)苯、雙(4-N,N-二乙基胺基-2-甲基苯基)-4-甲基苯基甲烷、2,7-雙(咔唑-9-基)-9,9-二辛基芴、4,4"-二(三苯基矽烷基)-p-三聯苯、4,4'-二(三苯基矽烷基)聯苯、9-(4-t-丁基苯基)-3,6-雙(三苯基矽烷基)-9H-咔唑、9-(4-t-丁基苯基)-3,6-二三苯甲基-9H-咔唑、9-(4-t-丁基苯基)-3,6-雙(9-(4-甲氧基苯基)-9H-芴-9-基)-9H-咔唑、2,6-雙(3-(9H-咔唑-9-基)苯基)吡啶、三苯基(4-(9-苯基-9H-芴-9-基)苯基)矽烷、9,9-二甲基-N,N-二苯基-7-(4-(1-苯基-1H-苯並[d]咪唑-2-基)苯基)-9H-芴-2-胺、3,5-雙(3-(9H-咔唑-9-基)苯基)吡啶、9,9-螺二芴-2-基-二苯基-膦氧化物、9,9'-(5-(三苯基矽烷基)-1,3-伸苯基)雙(9H-咔唑)、3-(2,7-雙(二苯基磷醯基)-9-苯基-9H-芴-9-基)-9-苯基-9H-咔唑、4,4,8,8,12,12-六(p-甲苯基)-4H-8H-12H-12C-氮雜二苯並[cd,mn]芘、4,7-二(9H-咔唑-9-基)-1,10-菲繞啉、2,2'-雙(4-(咔唑-9-基)苯基)聯苯、2,8-雙(二苯基磷醯基)二苯並[b,d]噻吩、雙(2-甲基苯基)二苯基矽烷、雙[3,5-二(9H-咔唑-9-基)苯基]二苯基矽烷、3,6-雙
(咔唑-9-基)-9-(2-乙基-己基)-9H-咔唑、3-(二苯基磷醯基)-9-(4-(二苯基磷醯基)苯基)-9H-咔唑、3,6-雙[(3,5-二苯基)苯基]-9-苯基咔唑等,可藉由與發光性摻雜劑共蒸鍍,形成發光層。
發光性摻雜劑方面,可舉例如3-(2-苯並噻唑
基)-7-(二乙基胺基)香豆素、2,3,6,7-四氫-1,1,7,7-四甲基-1H,5H,11H-10-(2-苯並噻唑基)喹嗪并[9,9a,1gh]香豆素、喹吖啶酮、N,N'-二甲基-喹吖啶酮、三(2-苯基吡啶)銥(III)(Ir(ppy)3)、雙(2-苯基吡啶)(乙醯基丙酮)銥(III)(Ir(ppy)2(acac))、三[2-(p-甲苯基)吡啶]銥(III)(Ir(mppy)3)、9,10-雙[N,N-二(p-甲苯基)胺基]蒽、9,10-雙[苯基(m-甲苯基)胺基]蒽、雙[2-(2-羥基苯基)苯並thiazolato]鋅(II)、N10,N10,N10,N10-四(p-甲苯基)-9,9'-二蒽-10,10'-二胺、N10,N10,N10,N10-四苯基-9,9'-二蒽-10,10'-二胺、N10,N10-二苯基-N10,N10-二萘基-9,9'-二蒽-10,10'-二胺、4,4'-雙(9-乙基-3-咔唑伸乙烯基)-1,1'-聯苯、苝、2,5,8,11-四-t-丁基苝、1,4-雙[2-(3-N-乙基咔唑)乙烯基]苯、4,4'-雙[4-(二-p-甲苯基胺基)苯乙烯基]聯苯、4-(二-p-甲苯基胺基)-4'-[(二-p-甲苯基胺基)苯乙烯基]茋、雙[3,5-二氟-2-(2-吡啶基)苯基-(2-羧基吡啶基)]銥(III)、4,4'-雙[4-(二苯基胺基)苯乙烯基]聯苯、雙(2,4-二氟苯基吡啶)四(1-吡唑基)硼酸酯銥(III)、N,N'-雙(萘-2-基)-N,N'-雙(苯基)-三(9,9-二甲基伸芴基)、2,7-雙{2-[苯基(m-甲苯基)胺基]-9,9-二甲基-芴-7-基}-9,9-二甲基-芴、N-(4-((E)-2-
(6((E)-4-(二苯基胺基)苯乙烯基)萘-2-基)乙烯基)苯基)-N-苯基苯胺、fac-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-叉-C,C2)、mer-銥(III)參(1-苯基-3-甲基苯並咪唑啉-2-叉-C,C2)、2,7-雙[4-(二苯基胺基)苯乙烯基]-9,9-螺二芴、6-甲基-2-(4-(9-(4-(6-甲基苯並[d]噻唑-2-基)苯基)蒽-10-基)苯基)苯並[d]噻唑、1,4-二[4-(N,N-二苯基)胺基]苯乙烯基苯、1,4-雙(4-(9H-咔唑-9-基)苯乙烯基)苯、(E)-6-(4-(二苯基胺基)苯乙烯基)-N,N-二苯基萘-2-胺、雙(2,4-二氟苯基吡啶)(5-(吡啶-2-基)-1H-四唑)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑)((2,4-二氟苄基)二苯基亞膦酸酯)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑特)(苄基二苯基亞膦酸酯)銥(III)、雙(1-(2,4-二氟苄基)-3-甲基苯並咪唑鎓)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)銥(III)、雙(3-三氟甲基-5-(2-吡啶基)吡唑特)(4',6'-二氟苯基吡啶酯)銥(III)、雙(4',6'-二氟苯基吡啶)(3,5-雙(三氟甲基)-2-(2'-吡啶基)吡咯)銥(III)、雙(4',6'-二氟苯基吡啶)(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)銥(III)、(Z)-6-基-N-(6-基喹啉-2(1H)-叉)喹啉-2-胺-BF2、(E)-2-(2-(4-(二甲基胺基)苯乙烯基)-6-甲基-4H-哌喃-4-叉)丙二腈、4-(二氰基伸甲基)-2-甲基-6-久洛尼定基-9-烯基-4H-哌喃、4-(二氰基伸甲基)-2-甲基-6-(1,1,7,7-四甲基久洛尼定基-9-烯基)-4H-哌喃、4-(二氰基伸甲基)-2-t-丁基-6-(1,1,7,7-四甲基久洛尼定基-4-基-乙烯基)-4H-哌喃、三(二苯甲醯基甲烷)菲繞啉銪(III)、5,6,11,12-四苯基丁省、雙(2-苯並[b]噻吩-2-基-吡啶)(乙醯
基丙酮)銥(III)、三(1-苯基異喹啉)銥(III)、雙(1-苯基異喹啉)(乙醯基丙酮)銥(III)、雙[1-(9,9-二甲基-9H-芴-2-基)-異喹啉](乙醯基丙酮)銥(III)、雙[2-(9,9-二甲基-9H-芴-2-基)喹啉](乙醯基丙酮)銥(III)、三[4,4'-二-t-丁基-(2,2')-二吡啶]釕(III).雙(六氟磷酸酯)、三(2-苯基喹啉)銥(III)、雙(2-苯基喹啉)(乙醯基丙酮)銥(III)、2,8-二-t-丁基-5,11-雙(4-t-丁基苯基)-6,12-二苯基四並苯、雙(2-苯基苯並thiazolato)(乙醯基丙酮)銥(III)、5,10,15,20-四苯基四苯並卟啉白金、鋨(II)雙(3-三氟甲基-5-(2-吡啶)-吡唑特)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-***)二苯基甲基膦、鋨(II)雙(3-(三氟甲基)-5-(2-吡啶基)-1,2,4-***)二甲基苯基膦、鋨(II)雙(3-(三氟甲基)-5-(4-t-丁基吡啶基)-1,2,4-***)二甲基苯基膦、雙[2-(4-n-己基苯基)喹啉](乙醯基丙酮)銥(III)、三[2-(4-n-己基苯基)喹啉]銥(III)、三[2-苯基-4-甲基喹啉]銥(III)、雙(2-苯基喹啉)(2-(3-甲基苯基)吡啶酯)銥(III)、雙(2-(9,9-二乙基-芴-2-基)-1-苯基-1H-苯並[d]咪唑(imidazolato)(乙醯基丙酮)銥(III)、雙(2-苯基吡啶)(3-(吡啶-2-基)-2H-色烯-2-歐尼)銥(III)、雙(2-苯基喹啉)(2,2,6,6-四甲基庚烷-3,5-二歐尼)銥(III)、雙(苯基異喹啉)(2,2,6,6-四甲基庚烷-3,5-二歐尼)銥(III)、銥(III)雙(4-苯基噻吩並[3,2-c]吡啶-N,C2)乙醯基丙酮、(E)-2-(2-t-丁基-6-(2-(2,6,6-三甲基-2,4,5,6-四氫-1H-吡咯并[3,2,1-iJ]喹啉-8-基)乙烯基)-4H-哌喃-4-叉)丙二腈、雙(3-三氟甲基-5-(1-異喹啉基)吡唑特)(甲基二苯基
膦)釕、雙[(4-n-己基苯基)異喹啉](乙醯基丙酮)銥(III)、白金(II)八乙基卟吩、雙(2-甲基二苯並[f,h]喹喔啉)(乙醯基丙酮)銥(III)、三[(4-n-己基苯基)羥基喹啉]銥(III)等。
形成電子輸送層/電洞阻隔層之材料方面,可
舉例如8-羥基喹啉-鋰、2,2',2"-(1,3,5-苄基甲苯基)-三(1-苯基-1-H-苯並咪唑)、2-(4-聯苯基)5-(4-t-丁基苯基)-1,3,4-噁二唑、2,9-二甲基-4,7-二苯基-1,10-菲繞啉、4,7-二苯基-1,10-菲繞啉、雙(2-甲基-8-喹啉)-4-(苯基酚化物)鋁、1,3-雙[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑5-基]苯、6,6'-雙[5-(聯苯基-4-基)-1,3,4-噁二唑2-基]-2,2'-二吡啶、3-(4-聯苯基)-4-苯基-5-t-丁基苯基-1,2,4-***、4-(萘-1-基)-3,5-二苯基-4H-1,2,4-***、2,9-雙(萘-2-基)-4,7-二苯基-1,10-菲繞啉、2,7-雙[2-(2,2'-二吡啶-6-基)-1,3,4-噁二唑5-基]-9,9-二甲基芴、1,3-雙[2-(4-t-丁基苯基)-1,3,4-噁二唑-5-基]苯、三(2,4,6-三甲基-3-(吡啶-3-基)苯基)硼烷、1-甲基-2-(4-(萘-2-基)苯基)-1H-咪唑[4,5F][1,10]菲繞啉、2-(萘-2-基)-4,7-二苯基-1,10-菲繞啉、苯基-二芘基膦氧化物、3,3',5,5'-四[(m-吡啶基)-苯-3-基]聯苯、1,3,5-三[(3-吡啶基)-苯-3-基]苯、4,4'-雙(4,6-二苯基-1,3,5-三嗪-2-基)聯苯、1,3-雙[3,5-二(吡啶-3-基)苯基]苯、雙(10-羥基苯並[h]喹啉)鈹、二苯基雙(4-(吡啶-3-基)苯基)矽烷、3,5-二(芘-1-基)吡啶等。
形成電子注入層的材料方面,可舉例如氧化鋰(Li2O)、氧化鎂(MgO)、氧化鋁(Al2O3)、氟化鋰(LiF)、
氟化鈉(NaF)、氟化鎂(MgF2)、氟化銫(CsF)、氟化鍶(SrF2)、三氧化鉬(MoO3)、鋁、Li(acac)、乙酸鋰、安息香酸鋰等。
陰極材料方面,可舉例如鋁、鎂-銀合金、鋁-鋰合金、鋰、鈉、鉀、銫等。
形成電子阻隔層的材料方面,可舉例如三(苯基吡唑)銥等。
使用本發明的電荷輸送性清漆之PLED元件的製作方法,雖不特別限定,可舉例如以下的方法。
上述OLED元件製作中,取代進行電洞輸送層、發光層、電子輸送層、電子注入層之真空蒸鍍操作,藉由依序形成電洞輸送性高分子層、發光性高分子層,可製作具有以本發明的電荷輸送性清漆形成的電荷輸送性薄膜之PLED元件。
具體上,於陽極基板上塗佈本發明的電荷輸送性清漆,以上述方法製作電洞注入層,於其上,依序形成電洞輸送性高分子層、發光性高分子層,進而蒸鍍陰極電極,作成PLED元件。
使用的陰極及陽極材料方面,可使用與上述OLED元件製作時同樣者,且可進行同樣的洗淨處理、表面處理。
電洞輸送性高分子層及發光性高分子層之形成法方面,可舉例如於電洞輸送性高分子材料或者發光性高分子材料、或此等中加入有摻雜劑之材料,添加溶劑進
行溶解、或均勻分散,並於電洞注入層或電洞輸送性高分子層之上塗佈後,各自燒成進行成膜之方法。
電洞輸送性高分子材料方面,可舉例如聚
[(9,9-二己基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[(9,9-二辛基芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,1'-伸二苯基-4,4-二胺)]、聚[(9,9-雙{1'-戊烯-5'-基}芴基-2,7-二基)-co-(N,N'-雙{p-丁基苯基}-1,4-二胺基伸苯基)]、聚[N,N'-雙(4-丁基苯基)-N,N'-雙(苯基)-聯苯胺]-以聚倍半矽氧烷封端、聚[(9,9-二辛基芴基-2,7-二基)-co-(4,4'-(N-(p-丁基苯基))二苯基胺)]等。
發光性高分子材料方面,可舉例如聚(9,9-二
烷基芴)(PDAF)等的聚芴衍生物、聚(2-甲氧基-5-(2'-乙基己氧基)-1,4-伸苯基伸乙烯基)(MEH-PPV)等的聚伸苯基伸乙烯基衍生物、聚(3-烷基噻吩)(PAT)等的聚噻吩衍生物、聚乙烯基咔唑(PVCz)等。
溶劑方面,可舉例如甲苯、二甲苯、氯仿
等,作為溶解或均勻分散法,可舉例如攪拌、加熱攪拌、超音波分散等的方法。
塗佈方法方面,非特別限定者,可舉例如噴
墨法、噴霧法、浸漬法、旋轉塗佈法、轉印印刷法、輥塗法、刷毛塗佈等。又,塗佈以在氮、氬等的惰性氣體下進行為佳。
燒成方法方面,可舉例如惰性氣體下或真空
中,以烤箱或加熱板進行加熱之方法。
又,不僅由上述電荷輸送性清漆得到的電荷
輸送性薄膜,由本發明的苯胺衍生物所得到的蒸鍍膜電荷輸送性亦優異,依用途亦可使用以蒸鍍法得到的電荷輸送性薄膜。
[實施例]
以下、舉合成例及實施例將本發明更具體說明,但本發明不限於下述實施例。又,使用之裝置如下。
(1)MALDI-TOF-MS:Bruker公司製、autoflex III smartbeam
(2)1H-NMR:日本電子(股)製、JNM-ECP300 FT NMR SYSTEM
(3)基板洗淨:長州產業(股)製、基板洗淨裝置(減壓電漿方式)
(4)清漆之塗佈:Mikasa(股)製、旋轉塗佈機MS-A100
(5)膜厚測定:(股)小坂研究所製、微細形狀測定機SurfcorderET-4000
(6)EL元件的製作:長州產業(股)製、多機能蒸鍍裝置系統C-E2L1G1-N
(7)EL元件的亮度等的測定:(有)Tech world製、I-V-L測定系統
(8)EL元件的壽命測定(半衰期的測定):(股)EHC製、有機EL亮度壽命評估系統PEL-105S
[合成例1]芳基磺酸化合物1的合成
將芳基磺酸化合物1(式(b1))依據國際公開第2006/025342號之記載,以下述反應式合成。
於充分乾燥的1-萘酚-3,6-二磺酸鈉
11g(31.59mmol)中,氮環境下,依序加入全氟聯苯4.797g(14.36mol)、碳酸鉀4.167g(30.15mol)及N,N-二甲基甲醯胺100mL,將反應系進行氮取代後,在內溫100℃進行6小時攪拌。
放冷至室溫後,為使反應後析出的芳基磺酸化合物1再溶解,再加入N,N-二甲基甲醯胺500mL,在室溫進行90分鐘攪拌。室溫攪拌後,使該溶液過濾,除去碳酸鉀殘渣,進行減壓濃縮。進而,為了除去殘存的雜質,於殘渣加入甲醇100mL,在室溫進行攪拌。
在室溫進行30分鐘攪拌後,將懸濁溶液過濾,得到過濾物。於過濾物中加入超純水300mL進行溶解,藉由使用陽離子交換樹脂DOWEX650C(陶氏化學公司製、H型約200mL、餾出溶劑:超純水)之管柱層析法進行離子交換。
將pH1以下的分劃在減壓下進行濃縮乾固,並使殘渣
在減壓下乾固而得到黃色粉末11g(收率85%)。
[實施例1-1]苯胺衍生物1的合成
將苯胺衍生物1(式(a1))用以下的方法進行合成。
燒瓶內,加入N-甲基-雙(4-胺基苯基)胺
5.02g、溴三苯基胺16.03g(2.1eq)、Pd2(dba)30.11g(0.5mol%)、P(t-Bu)30.24g(5.0mol%)、t-丁氧基鈉(t-BuONa)4.75g(2.1eq)及甲苯50g,進行氮取代後,在迴流條件下進行3小時攪拌。
將反應液放冷至室溫後,於其中加入離子交換水及乙酸乙基酯進行分液處理,將得到的有機層以硫酸鎂乾燥。
之後,使溶劑進行減壓餾去,使得到的殘渣溶於二噁烷及異丙醇之混合溶劑(1/4(v/v)),藉由將該溶液滴入甲醇進行再沉澱。
將以過濾回收的沉澱物以乙酸乙基酯洗淨,減壓加熱下充分乾燥,得到苯胺衍生物1(收量:12g、收率:73%)。1H-NMR的測定結果如以下所示。
1H-NMR(300MHz,DMSO-d6)δ[ppm]:7.94(s,2H),7.21-7.25(t,8H),6.86-7.02(m,28H),3.17(s,3H).
[實施例1-2]苯胺衍生物2之合成
(1)N,N-二苯基-p-伸苯基二胺(式(13))用以下的方法進行合成。
燒瓶內,加入溴三苯基胺4.04g及Pd(dba)2
0.358g(5mol%)後進行氮取代。於其中依序加入甲苯40mL、P(t-Bu)3之甲苯溶液5.24mL(24.02g/L、5mol%)及鋰六甲基二矽氮烷化物(LHMDS)17.1mL(1.09M、1.5eq)後,在室溫進行4小時攪拌,再於其中加入適量的三氟乙酸後進行整夜攪拌。
攪拌完畢後,使用2mol/L氫氧化鈉水溶液30mL進行分液處理,並將得到的有機層以離子交換水進行2次洗淨。洗淨後,將該有機層以硫酸鈉進行乾燥,於乾燥的有機層加入活性碳0.4g,在室溫進行40分鐘攪拌。之後,除去活性碳後使有機溶劑減壓餾去。
由得到的殘渣,使用甲苯4.3g與己烷12.9g進行再結晶,使經過濾回收的析出物充分乾燥,得到N,N-二苯基-p-伸苯基二胺(收量:2.41g、收率:74%)。
(2)苯胺衍生物2(式(a13))用以下的方法進行合
成。
燒瓶內,加入N,N-雙(p-溴苯基)苯胺1.35g、
N,N-二苯基-p-伸苯基二胺1.91g(2.2eq)、Pd(PPh3)40.193g(5mol%)、t-BuONa0.713g(2.2eq)及二甲苯20mL,進行氮取代後,在迴流條件下進行3.5小時攪拌。攪拌完畢後,使反應液放冷至室溫,於其中加入離子交換水及氯仿,進行分液處理。
接著,使得到的有機層以硫酸鈉進行乾燥,之後,減壓下將溶劑餾去,使得到的殘渣完全溶解於加熱至80℃的1,4-二噁烷(12.5g)。於其中加入活性碳0.14g後,進行30分鐘攪拌,攪拌完畢後,使活性碳以加熱過濾除去,從得到的濾液將有機溶劑減壓餾去。將得到的殘渣溶於甲苯25g,進行管柱層析法,藉由以薄層層析法(TLC)法等確認目的物之有無,取得含目的物之分劃。
由取出的分劃在減壓下將溶劑餾去後,將得到的殘渣溶解於加熱至90℃的甲苯(15.3g),將該溶液冷卻至0℃,使經過濾回收的析出物充分乾燥,得到苯胺衍生物2(收量:1.14g、收率:45%)。1H-NMR及MALDI-TOF-MS的測定結果如以下所示。
1H-NMR(300MHz,DMSO-d6)δ[ppm]:8.09(s,2H),7.21-7.26(m,11H),6.91-7.04(m,30H).
MALDI-TOF-MS m/Z found:761.72([M]+calcd:761.35)
[實施例1-3]苯胺衍生物3之合成
苯胺衍生物3(式(a24))用以下的方法進行合成。
於燒瓶內,加入三(4-胺基苯基)胺1.46g、溴
三苯基胺5.35g(3.3eq)、Pd(PPh3)40.299g(5mol%)、t-BuONa1.59g(3.3eq)及二甲苯50mL,進行氮取代後,在迴流條件下進行8小時攪拌。攪拌完畢後,將反應液放冷至室溫,於其中加入氯仿50mL後進行矽藻土過濾。
接著,使用該濾液與飽和食鹽水,進行分液處理,將得到的有機層以硫酸鈉進行乾燥後,減壓下將溶劑餾去,使用得到的殘渣及氯仿,進行短管柱層析。
在得到的溶液加入活性碳0.5g,進行30分鐘攪拌,使該活性碳以過濾除去。將由該濾液使溶劑餾去所得的殘渣溶於氯仿與n-己烷的混合溶劑(1/1(v/v))。
使用得到的溶液,進行管柱層析法,藉由以TLC法等確認目的物之有無,取出含有目的物之分劃後,使該溶劑減壓餾去。
於溶解有得到的殘渣的甲苯溶液中加入n-己烷,進行再沉澱,使以過濾回收的沉澱物在減壓下充分乾燥,得到苯胺衍生物3(收量:2.01g、收率:39%)。MALDI-TOF-MS的測定結果如以下所示。
MALDI-TOF-MS m/Z found:1019.98([M]+calcd:1019.47)
[實施例2-1]
將苯胺衍生物1 0.062g與磷鎢酸(PTA)0.309g在氮環境下溶於1,3-二甲基-2-咪唑啉酮(DMI)4g。於得到的溶液中,加入環己醇(CHA)6g及丙二醇(PG)2g進行攪拌,調製電荷輸送性清漆。
[實施例2-2]
除苯胺衍生物1及PTA的使用量各自為0.053g及0.318g以外,以與實施例2-1同樣的方法調製電荷輸送性清漆。
[實施例2-3]
使苯胺衍生物2 0.062g與PTA0.309g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g進行攪拌,調製電荷輸送性清漆。
[實施例2-4]
除苯胺衍生物2及PTA的使用量各自為0.053g及0.318g以外,以與實施例2-3同樣的方法調製電荷輸送性清漆。
[實施例2-5]
使苯胺衍生物3 0.062g與PTA0.309g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,調製電荷輸送性清漆。
[實施例2-6]
除苯胺衍生物3及PTA的使用量各自為0.053g及0.318g以外,以與實施例2-5同樣的方法調製電荷輸送性清漆。
[實施例3-1]
使苯胺衍生物1 0.083g與芳基磺酸化合物1 0.161g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,調製電荷輸送性清漆。
[實施例3-2]
使苯胺衍生物2 0.088g與芳基磺酸化合物1 0.157g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,調製電荷輸送性清漆。
[實施例3-3]
除苯胺衍生物2及芳基磺酸化合物1的使用量各自為0.073g及0.172g以外,以與實施例3-2同樣的方法調製電荷輸送性清漆。
[實施例3-4]
使苯胺衍生物3 0.082g與芳基磺酸化合物1 0.163g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,調製電荷輸送性清漆。
[實施例3-5]
除苯胺衍生物3及芳基磺酸化合物1的使用量各自為0.067g及0.178g以外,以與實施例3-4同樣的方法調製電荷輸送性清漆。
[實施例4-1]
使苯胺衍生物1 0.107g與芳基磺酸化合物1 0.138g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,於其中加入3,3,3-三氟丙基三甲氧基矽烷0.016g及苯基三甲氧基矽烷0.008g進而攪拌,調製電荷輸送性清漆。
[實施例4-2]
除苯胺衍生物1及芳基磺酸化合物1的使用量各自為
0.083g及0.161g以外,以與實施例4-1同樣的方法調製電荷輸送性清漆。
[實施例4-3]
使苯胺衍生物2 0.112g與芳基磺酸化合物1 0.133g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,於其中加入3,3,3-三氟丙基三甲氧基矽烷0.016g及苯基三甲氧基矽烷0.008g後進而攪拌,調製電荷輸送性清漆。
[實施例4-4及4-5]
除苯胺衍生物2及芳基磺酸化合物1的使用量各自為0.088g及0.157g(實施例4-4)、0.073g及0.172g(實施例4-5)以外,以與實施例4-3同樣的方法調製電荷輸送性清漆。
[實施例4-6]
使苯胺衍生物3 0.105g與芳基磺酸化合物1 0.140g在氮環境下溶於DMI4g。於得到的溶液中加入CHA6g及PG2g後進行攪拌,於其中加入3,3,3-三氟丙基三甲氧基矽烷0.016g及苯基三甲氧基矽烷0.008g進而攪拌,調製電荷輸送性清漆。
[實施例4-7及4-8]
除苯胺衍生物3及芳基磺酸化合物1的使用量各自為0.082g及0.163g(實施例4-7)、0.067g及0.178g(實施例4-8)以外,以與實施例4-6同樣的方法調製電荷輸送性清漆。
[實施例5]
將實施例2-1~4-8所得到的清漆各自使用旋轉塗佈機塗佈於ITO基板後,在50℃進行5分鐘乾燥,進而,大氣環境下、在230℃進行15分鐘燒成,於ITO基板上形成30nm之均勻的薄膜。作為ITO基板使用銦錫氧化物(ITO)在表面上以膜厚150nm圖案化的25mm×25mm×0.7t之玻璃基板,使用前以O2電漿洗淨裝置(150W、30秒鐘)將表面上的雜質除去。
接著,對形成薄膜的ITO基板,使用蒸鍍裝置(真空度1.0×10-5Pa),依序層合N,N'-二(1-萘基)-N,N'-二苯基聯苯胺(α-NPD)、三(8-羥基喹啉)鋁(III)(Alq3)、氟化鋰、及鋁的薄膜,得到有機EL元件。此時,蒸鍍速率,α-NPD、Alq3及鋁以0.2nm/秒,氟化鋰以0.02nm/秒的條件各自進行,膜厚各自為30nm、40nm、0.5nm及120nm。
又,為了防止空氣中之氧、水等的影響造成特性劣化,有機EL元件以密封基板密封後,評估其特性。密封用以下的順序進行。
氧濃度2ppm以下、露點-85℃以下的氮環境中,將有機EL元件收納於密封基板間,使密封基板以接著材
(Nagasechemtex(股)製、XNR5516Z-B1)貼合。此時,使捕水劑(Dynic(股)製、HD-071010W-40)與有機EL元件一同收納於密封基板內。
對貼合的密封基板,照射UV光(波長:365nm、照射量:6,000mJ/cm2)後,在80℃進行1小時退火處理,使接著材硬化。
對此等之元件測定驅動電壓5V之電流密度及亮度。
使用實施例2-1~2-6的清漆製作的元件的結果如表1,使用實施例3-1~3-6的清漆製作的元件的結果如表2,使用實施例4-1~4-8的清漆製作的元件的結果如表3所示。
如表1所示般,使用本發明的含有苯胺衍生
物與磷鎢酸之電荷輸送性清漆的場合,可製造能實現具有優異的電特性之EL元件之作為電洞注入層的較佳的電荷輸送性薄膜。
如表2所示般,即使使用本發明的含有苯胺
衍生物與芳基磺酸化合物之電荷輸送性清漆的場合,可製造能實現具有優異的電特性之EL元件之作為電洞注入層的較佳的電荷輸送性薄膜。
如表3所示般,即使使用本發明的含有苯胺
衍生物與芳基磺酸化合物與有機矽烷化合物之電荷輸送性清漆的場合,可製造能實現具有優異的電特性之EL元件之作為電洞注入層的較佳的電荷輸送性薄膜。
又,進行使用實施例2-5、2-6、3-1~3-5及
4-1~4-8之清漆製作的元件的耐久性試驗。亮度的半衰期(初期亮度5,000cd/m2)如表4所示。
如表4示般,具備由本發明之電荷輸送性清漆所得到的電荷輸送性薄膜之有機EL元件耐久性優異。
Claims (15)
- 一種苯胺衍生物,其特徵係以式(1)表示,
- 如請求項1記載之苯胺衍生物,其中,R2~R37為氫原子、鹵素原子、以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或-OY2基。
- 如請求項1或2記載之苯胺衍生物,其中,R1為以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或式(2)所表示之基。
- 如請求項3記載之苯胺衍生物,其中,R1為式(2)所表示之基。
- 如請求項4記載之苯胺衍生物,其中,R38~R55為氫原子、鹵素原子、以Z1取代亦可的碳數1~20之烷基、以Z2取代亦可的碳數6~20之芳基或-OY2基。
- 一種電荷輸送性物質,其特徵係由請求項1~5之任1項記載之苯胺衍生物所構成。
- 一種電荷輸送性清漆,其特徵係含有請求項1~5之任1項記載之苯胺衍生物、摻雜劑及有機溶劑。
- 一種電荷輸送性薄膜,其特徵係使用請求項7記載的電荷輸送性清漆來製作。
- 一種電荷輸送性薄膜,其特徵係含有請求項1~5之任1項記載之苯胺衍生物。
- 一種電子裝置,其特徵係具備至少1層請求項8或9記載的電荷輸送性薄膜。
- 一種有機電致發光元件,其特徵係具備至少1層請求項8或9記載的電荷輸送性薄膜。
- 如請求項11記載之有機電致發光元件,其中,前述電荷輸送性薄膜為電洞注入層或電洞輸送層。
- 一種請求項1記載之苯胺衍生物之製造方法,其特徵係使式(3)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物在觸媒存在下進行反應,
- 一種請求項1記載之苯胺衍生物之製造方法,其特徵係使式(6)所表示之胺化合物與式(7)所表示之胺化合物與式(8)所表示之胺化合物在觸媒存在下進行反應,
- 一種請求項4記載之苯胺衍生物之製造方法,其特徵係使式(9)所表示之胺化合物與式(4)所表示之胺化合物與式(5)所表示之胺化合物與式(10)所表示之胺化合物在觸媒存在下進行反應,
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- 2014-06-17 KR KR1020167001186A patent/KR102257209B1/ko active IP Right Grant
- 2014-06-17 EP EP14813882.9A patent/EP3012245B1/en not_active Expired - Fee Related
- 2014-06-17 WO PCT/JP2014/065999 patent/WO2014203882A1/ja active Application Filing
- 2014-06-20 TW TW103121348A patent/TWI603946B/zh active
Also Published As
Publication number | Publication date |
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KR20160021447A (ko) | 2016-02-25 |
US20160141507A1 (en) | 2016-05-19 |
EP3012245B1 (en) | 2018-08-08 |
EP3012245A1 (en) | 2016-04-27 |
TW201512154A (zh) | 2015-04-01 |
CN105324360B (zh) | 2018-06-22 |
JPWO2014203882A1 (ja) | 2017-02-23 |
CN105324360A (zh) | 2016-02-10 |
US10164196B2 (en) | 2018-12-25 |
KR102257209B1 (ko) | 2021-05-27 |
EP3012245A4 (en) | 2017-01-25 |
WO2014203882A1 (ja) | 2014-12-24 |
JP6061034B2 (ja) | 2017-01-18 |
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